You are probably reading this article at work or at home.  Either way, it’s likely that you’re not reading this while at a Caribbean destination.  Glancing through this blog and across the internet you’ll find seductive photos and video of blue water edged by soft white sand beaches backdropped with lush tropical vegetation.  It’s easy to daydream about being there feeling the warm sun kiss your skin and hearing the methodical rhythm of waves rolling in against the beach.  This is how I escaped mentally while living the day to day grind.  That is until I actually started getting out there more. 

Let’s face it, life happens.  Work, kids, and relationships are all common items in life that keep you in a steady routine of the familiar.  You probably pick up hobbies that you can fill in around this daily, weekly, and monthly rhythm.  This is where Ashley and I were when we realized we wanted to escape the old rhythm and begin to explore the warm waters of the Caribbean.  We’ve gone from traveling once a year (if we were lucky) to heading out sometimes every other month.  We work, we have 3 young kids, and we’re certainly not rich.  Here is how we do it!

Decide to Go!

It sounds trivial but we had to sit down and talk about if it was what we really wanted.  We knew it would mean giving up a few things, like eating out as often and not buying as much meaningless crap, but we were willing to do what we needed to start getting down to tropical waters.  Once we were decidedly on the same page it was time to figure out where the first trip would be.

Plan Ahead and Work Within Your Budget

We’ve been fortunate enough to have taken some amazing and exclusive trips.  However, we knew that if we wanted to make traveling a more reoccurring adventure we would need to make most of travel deals and our time.  We actually calculated what our annual travel budget would be and then broke it down by the number of trips we could take.  Our first year of trying this we budgeted $500/month ($6000/year).  I was working feverishly and it was difficult for me to take a single day off, on top of that we had 3 young kids.  So, for our first year we decided we’d do 3 trips with a budget of around $2,000/trip.  We would do this by leaving on a Thursday and coming back on Sunday.  Three day trips were cheap and were at our max comfort zone for leaving the kiddos.  That first year we went to Cozumel, Belize, and Rhoatan!  Each trip was right at our budget, including airfare, diving, food, and drinks.

Decide on the type of trip you want!

There are a number of ways to explore the Caribbean and there is no magical way that’s better than any of the others.  As you can see from above, we have decided that we prefer staying in a resort.  During our first year, 2 of the 3 resorts we stayed in were all inclusive.  

• All Inclusive Vacations – This is pushing the easy button and one of our favorite ways to travel, especially if it’s your first time going somewhere.  Some people are more adventurous and want to eat local flavor for every meal.  Although we do enjoy eating local cuisine it’s nice to know you have a fall back plan at an all inclusive.  It also makes it easy to budget.
• Cruises – This is another easy button.  On top of traveling to 2-4 destinations there are a number of activities on the vessel to take part in.  Food is all included but unlike all inclusive resorts, you’ll pay a hefty bar tab if you’re into that sort of thing.  I’ve been on a number of cruises and I had a great time.  I did began to wish I was at the actual destination longer though, which is why we prefer resort staying now.
• AirBNB – This is an awesome way to see a new places and provides a greater variety of comfort levels.  You can stay for way cheaper or get much more exclusive.  Some of the high end places can come with Chefs and maid services.  This option typically takes a bit more planning as there isn’t routine travel to and from the airports and you’ll need to figure out what you’ll do for food.

Know where to look for deals!

OK, so you’ve got your budget and you know how you want to travel.   Where the heck are all of the deals?  Everyone seems to be advertising cheap caribbean vacations but there aren’t a lot of really amazing deals.  We’ve booked vacations through CheapCaribbean as well as through GrouponGetaways.  Honestly, we’ve never booked an AirBnb but it is something we’ll be trying soon.  It seems like the best deals we’ve found have been through Groupon.  Sometimes we don’t want to go during the times they’ve made available through Groupon, in that case we’ve contacted the resort directly and asked if they’d honor the same groupon deal at another time and 2 out of 3 times it worked!

Have you found deals getting around the Caribbean?  Comment Below and tell us what they are!  

Have Questions about Caribbean Travel?  Ask us anything and we’ll help out anywhere we can! 

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